PL206420B1 - New derivatives of disorbityl-amine and method for their obtaining - Google Patents

Description

(12) PATENT DESCRIPTION (19) PL (11) 206420 (13) B1 (21) Application number: 380363 ^{(51) Int.Cl.}

C07C 215/04 (2006.01) (22) Filed on: 03/08/2006

New derivatives of disorbitylamine and the method of their preparation (73) The right holder of the patent:

POLITECHNIKA WROCŁAWSKA, Wrocław, PL (43) Application was announced:

04.02.2008 BUP 03/08 (72) Inventor (s):

KAZIMIERA WILK, Wrocław, PL URSZULA LASKA, Świdnica, PL BARBARA MATUSZEWSKA, Wrocław, PL JERZY DĄBROWSKI, Wrocław, PL LUDWIK SYPER, Wrocław, PL (45) The grant of the patent was announced:

August 31, 2010 WUP 08/10 (74) Proxy:

item. stalemate. Winohradnik Halina

Wroclaw University of Science and Technology

Intellectual Property Protection and Patent Information Office

PL 206 420 B1

Description of the invention

The subject of the invention is new disorbitylamine derivatives belonging to the non-ionic sugar surfactants of the dicephalic type. The invention also relates to a process for the preparation of novel disorbitylamine derivatives.

The new disorbitylamine derivatives belong to the new generation of surfactants, characterized by low environmental impact and human-friendly physiological properties. Sugar dicephalic surfactants are known, inter alia, from US Patent No. 5,270,161 and from PC Griffiths, ML Whatton, RJ Abbott, W. Kwan, AR Pitt, AM Howe, SM King, RK Heenan, J. Colloid Interface Sci. , 215, 114, 1999; B. L. Bales, R. Ranganathan, P. C. Griffiths, J. Phys. Chem. B, 105, 7465,2001; K. A. Wilk, L. Syper, B. Burczyk, A. Sokołowski, B. W. Domagalska, J. Surfact. Deterg., 3, 2, 185, 2000.

From the Polish patent application no. P 331 294 there are known aldonamidoamines with the name N-alkyl-N, N-bis [3- (aldonamido) propyl] amines. From another Polish patent application No. P 358 723, diamidoamines are known to be derivatives of long-chain aliphatic amines called N-alkyl-N, N-bis- [2 - {[3-N, N-dimethylamino) propyl] amido} ethyl} amines.

A characteristic feature of these compounds is a very complex hydrophilic group of the molecule, which consists of two sugar moieties of the same type linked by a bond to which is also attached a single hydrocarbon chain being a hydrophobic moiety. These surfactants show a very high surface activity compared to compounds containing one hydrophilic group and one hydrophobic group per molecule; have a low critical concentration of micellization. Compared to conventional surfactants, dicephalic compounds are more efficient in the micelle formation process, as indicated by several orders of magnitude lower cmc values.

The invention relates to new disorbitylamine derivatives which are N-alkyl-N, N-dialdithylamines of the general formula I, in which R is a straight or branched, saturated or unsaturated n-alkyl chain containing from 6 to 20 carbon atoms, and Y is an atom. hydrogen.

The new N-alkyl-N, N-dialdithylamines of the general formula 1 is obtained by the process of the invention, which consists in that N, N-dialdithylamines of the formula 2, in which Y is a hydrogen atom, are reacted in a one-step reaction with the alkyl bromides of the formula Is a straight or branched, saturated or unsaturated n-alkyl chain containing from 6 to 20 carbon atoms, preferably from 8 to 16, in methanol, in the presence of a catalyst, preferably K2CO3, under a nitrogen atmosphere.

The compounds according to the invention can find use as active ingredients of pharmaceutical and cosmetic formulations, as components of washing, washing and cleaning agents, and also in the food industry as emulsifiers. For their production, a renewable resource base is used more and more often.

The subject of the invention is explained in the examples of the preparation of new N-alkyl-N, N-dialdithylamines surfactants.

P r z k ł a d I

1.0 g of K 2 CO 3 catalyst is placed in the reactor and heated to 125 ° C under a nitrogen atmosphere. Then 3.5 g of N, N-diglucitylamine represented by the formula 2 in which Y = H and 1.9 g of the bromide of the formula III in which R is the n-octyl chain are introduced. The system is stirred under nitrogen at 100-120 ° C for 65 hours. The mixture is then dissolved in methanol and the catalyst is removed by filtration under reduced pressure. After evaporating the solvent, the product is obtained in 72% yield with the structure shown in the formula 1, in which Y = H and R is the n-octyl chain.

summary formula C20H43NO10;

molecular weight 457.64 gmol ^-1 ; C, H, N content:

calculated, respectively: 52.49; 9.49; 3.06; appointed, respectively: 52.44; 9.43; 3.10; Krafft point = <0 ° C;

surface tension of 0.01% aqueous solution in distilled water = 32.80 mNm ^-1 ;

HLB = 12.99;

contact angle = 83.7 °.

PL 206 420 B1

P r z x l a d II

1.0 g of K 2 CO 3 catalyst is placed in the reactor and heated to 125 ° C under a nitrogen atmosphere. Then 3.5 g of N, N-diglucitylamine represented by the formula 2 in which Y = H and 2.2 g of the bromide of the formula III in which R is the n-decyl chain are introduced. The system is stirred under nitrogen at 100-120 ° C for 60 hours. The mixture is then dissolved in methanol and the catalyst is removed by filtration under reduced pressure. After evaporating the solvent, the product is obtained in 65% yield with the structure shown in the formula 1, in which Y = H and R is an n-decyl chain.

Summary formula C22H47NO10;

molecular weight 485.70 gmol ^-1 ; C, H, N content:

calculated, respectively: 54.40; 9.77; 2.88; designated, respectively: 54.39; 9.73; 2.94; Krafft point = <0 ° C;

surface tension of 0.01% aqueous solution in distilled water = 43.12 mNm ^-1 ;

HLB = 12.04;

contact angle = 83.2 °.

P r z x l a d III

1.0 g of K 2 CO 3 catalyst is placed in the reactor and heated to 125 ° C under a nitrogen atmosphere. Then 3.5 g of N, N-diglucitylamine represented by the formula 2 in which Y = H and 2.5 g of the bromide of the formula III in which R is the n-dodecyl chain are introduced. The system is stirred under nitrogen at 100-120 ° C for 56 hours. The mixture was then dissolved in methanol and the catalyst was removed by filtration under reduced pressure. After evaporating the solvent, the product is obtained in 80% yield with the structure shown in the formula 1, in which Y = H and R is an n-dodecyl chain.

Summary formula C24H51NO10;

molecular weight 513.76 gmol ^-1 ; C, H, N content:

calculated, respectively: 56.10; 10.02; 2.73; designated, respectively: 56.05; 9.97; 2.77; Krafft point = 7 ° C;

surface tension of 0.01% aqueous solution in distilled water = 34.42 mNm ^-1 ;

HLB = 11.09;

contact angle = 81.9 °.

P r x l a d IV

1.0 g of K 2 CO 3 catalyst is placed in the reactor and heated to 125 ° C under a nitrogen atmosphere. Then 3.5 g of N, N-diglucitylamine represented by the formula 2 in which Y = H and 2.8 g of the bromide of the formula III in which R is the n-tetradecyl chain are introduced. The system is stirred under nitrogen at 100-120 ° C for 55 hours. The mixture was then dissolved in methanol and the catalyst was removed by filtration under reduced pressure. After evaporating the solvent, the product is obtained in 81% yield with the structure shown in the formula 1, in which Y = H and R is an n-tetradecyl chain.

Summary formula C26H55NO10;

molecular weight 541.82 gmol ^-1 ; C, H, N content:

calculated respectively: 57.63; 10.25; 2.59; appointed, respectively: 57.58; 10.19; 2.63; Krafft point = 15 ° C;

surface tension of 0.01% aqueous solution in distilled water = 44.04 mNm ^-1 ;

HLB = 10.14;

contact angle = 80.3 °.

P r z k ł a d V

1.0 g of K 2 CO 3 catalyst is placed in the reactor and heated to 125 ° C under a nitrogen atmosphere. Then 3.5 g of N, N-diglucitylamine represented by the formula 2 in which Y = H and 3.1 g of the bromide of the formula III in which R is the n-hexadecyl chain are introduced. The system is stirred under nitrogen at 100-120 ° C for 47 hours. The mixture is then dissolved in methanol

And the catalyst is removed by filtration under reduced pressure. After evaporating the solvent, the product is obtained in 88% yield with the structure shown in the formula 1, in which Y = H and R is the n-tetradecyl chain.

Summary formula C28H59NO10;

molecular weight 569.88 gmol ^-1 ; C, H, N content:

calculated respectively: 59.01; 10.46; 2.46; designated, respectively: 58.96; 10.40; 2.50; Krafft point = 23 ° C;

surface tension of 0.01% aqueous solution in distilled water = 40.96 mNm ^-1 ;

HLB = 9.19;

contact angle = 85 ° C.

Claims (2)

Patent claims 1.New disorbitylamine derivatives, which are N-alkyl-N, N-dialditylamine of the general formula I, in which R is a straight or branched, saturated or unsaturated n-alkyl chain containing from 6 to 20 carbon atoms, while Y is an atom hydrogen. 2. A method for the preparation of new N-alkyl-N, N-dialdithylamines of the general formula I, in which R is a straight or branched, saturated or unsaturated n-alkyl chain containing from 6 to 20 carbon atoms, and Y is a hydrogen atom, characterized by in that the N, N-dialdithylamines of formula 2 in which Y is hydrogen is reacted in a one-step reaction with alkyl bromides of formula 3 in which R is a straight or branched, saturated or unsaturated n-alkyl chain containing from 6 to 20 carbon atoms, preferably from 8 to 16, in methanol, in the presence of a catalyst, preferably K2CO3, under a nitrogen atmosphere.